Moisture-curable composition and cured product

Abstract

The purpose of this invention is to provide a moisture-curing composition that exhibits high elongation, high strength, and excellent heat resistance after curing. This invention provides a moisture-curing composition containing the following components (A) to (C): (A) an organic polymer having two or more alkoxysilyl groups within its molecule; (B) an organometallic catalyst; and (C) an aromatic secondary amine compound.

Description

Technical Field

[0001] This invention relates to a moisture-curing composition with excellent heat resistance and the cured product thereof. Background Technology

[0002] In recent years, from a lightweighting perspective, aluminum has been widely used as a component in automotive batteries, as described in Japanese Patent Application Publication No. 2022-175357. Furthermore, to improve battery production efficiency, heat sources such as waste hot air drying ovens are required during manufacturing. Therefore, sealants and adhesives used in batteries are required to be moisture-curing and room-temperature curing. Additionally, due to heat generation and external environmental influences, the internal temperature of the battery becomes high; therefore, sealants and adhesives used in batteries require heat resistance and other durability properties. Summary of the Invention

[0003] However, in the past, although the cured products of wet-curing compositions had high elongation and high strength, the rubber properties of the cured products changed greatly due to thermal degradation, which was insufficient in terms of heat resistance.

[0004] Therefore, the object of the present invention is to provide a moisture-curing composition that has high elongation, high strength and excellent heat resistance.

[0005] The main idea of ​​this invention will now be described. This invention overcomes the aforementioned problems of the prior art.

[0006] The main idea of ​​the present invention will now be described. A first aspect of the present invention is a moisture-curing composition comprising the following components (A) to (C). (A) Composition: An organic polymer containing two or more alkoxysilyl groups within its molecule. (B) Components: Organometallic catalyst, (C) Components: Aromatic secondary amine compounds.

[0007] The second aspect of the present invention is the moisture-curing composition described in the first aspect, wherein the metal of the above-mentioned component (B) is one or more selected from the group consisting of zinc, titanium and tin.

[0008] The third aspect of the present invention is the moisture-curing composition described in the second aspect, wherein the metal of the above-mentioned component (B) is zinc.

[0009] The fourth aspect of the present invention is a moisture-curing composition as described in any one of the first to third aspects, wherein the component (C) described above has any one of the structures of general formulas 1 to 3 described below.

[0010] The fifth aspect of the present invention is a moisture-curing composition as described in any one of the first to fourth aspects, wherein the above-mentioned component (C) comprises N,N'-di-2-naphthyl-p-phenylenediamine or 4,4'-bis(α,α-dimethylbenzyl)diphenylamine.

[0011] The sixth aspect of the present invention is a moisture-curing composition as described in any one of the first to fifth aspects, wherein the main chain of the organic polymer of the above-mentioned component (A) is polyoxyethylene or poly(meth)acrylate.

[0012] The seventh aspect of the present invention is a moisture-curing composition as described in any one of the first to sixth aspects, wherein the organic polymer of component (A) is linear and has alkoxysilyl groups at both ends.

[0013] The eighth aspect of the present invention is a moisture-curing composition as described in any one of the first to seventh aspects, wherein the content of component (C) is 0.01 to 20 parts by mass relative to 100 parts by mass of component (A).

[0014] The ninth aspect of the present invention is a cured product, which is formed by curing the wet-curing composition of any one of the first to eighth aspects. Detailed Implementation

[0015] One aspect of the present invention is a moisture-curing composition comprising the following components (A) to (C). (A) Composition: An organic polymer containing two or more alkoxysilyl groups within its molecule. (B) Components: Organometallic catalyst, (C) Components: Aromatic secondary amine compounds.

[0016] The cured product of the moisture-curing composition of the present invention has high elongation, high strength and excellent heat resistance.

[0017] The present invention will now be described in detail. It should be noted that, for the expression "X~Y" used in this specification, X and Y refer to numerical values, and are used to respectively include X and Y as lower and upper limits. Furthermore, in the present invention, (meth)acrylate refers to both acrylate and methacrylate.

[0018] <(A) ingredient>

[0019] The component (A) that can be used in this invention is an organic polymer having two or more alkoxysilyl groups within its molecule. Particularly from the perspective of achieving higher elongation, higher strength, and superior tensile shear bond strength to aluminum in the cured product, the organic polymer is preferably linear and has alkoxysilyl groups at both ends. The alkoxysilyl groups undergo a crosslinking reaction via component (B) described later and moisture (water) entering the moisture-curing composition from outside air. Specific examples of component (A) include components where the main chain of the organic polymer in component (A-1) is a polyoxyethylene compound, and components where the main chain of the organic polymer in component (A-2) is a poly(meth)acrylate compound. Considering heat resistance, component (A-1) is preferred.

[0020] Examples of alkoxysilyl groups used as component (A) include trimethoxysilyl, triethoxysilyl, triisopropoxysilyl, etc.; dialkoxysilyl groups such as methyldimethoxysilyl, methyldiethoxysilyl, etc.; and monoalkoxysilyl groups such as dimethylmethoxysilyl, dimethylethoxysilyl, etc. From the perspective of superior heat resistance of the cured product, dialkoxysilyl or trialkoxysilyl groups are preferred as component (A), with trimethoxysilyl or triethoxysilyl groups being the most preferred.

[0021] From a treatment point of view, component (A) is preferably in a liquid state at 25°C. The viscosity of component (A) at 25°C is preferably 0.5~500 Pa·s, more preferably 1~200 Pa·s, even more preferably 3~150 Pa·s, and even more preferably 10~100 Pa·s. By achieving a viscosity of 0.5~500 Pa·s, the cured product exhibits higher elongation, higher strength, and superior tensile shear bond strength to aluminum. It should be noted that, unless otherwise specified, the viscosity is measured using a cone-plate viscometer at 25°C according to JIS K 6833-1:2008.

[0022] Commercially available products containing the aforementioned ingredient (A-1) are not particularly limited, and examples include SAT010, SAX115, SAT030, SAT200, SAT350, SAT400, SAX220, SAX510, SAX520, SAX530, SAX575, SAX580, SAX710, SAX720, SAX725, SAX750, SAX770, S203, S303, S203H, S303H, S943S, S911S, MA440, MA447, MA451, MA903, MA903M, MA904, S943, MAX923, MAX951, etc., manufactured by KANEKA CORPORATION, but are not limited to these.

[0023] Commercially available products containing the aforementioned ingredient (A-2) include SA110S, SA100S, SA120S, and OR110S manufactured by KANEKA CORPORATION, but are not limited to these.

[0024] <(B) Components>

[0025] The component (B) that can be used in this invention is an organometallic catalyst. Component (B) is a catalyst for curing the moisture-curing composition. Component (B) promotes the dealcoholization condensation of components (A) with each other, and with silane compounds having alkoxysilyl groups (excluding component (A)) described later, and silane compounds having alkoxysilyl groups (excluding component (A)) with each other. Specific examples of component (B) as a curing catalyst include organotin catalysts, organotitanium catalysts, organozirconium catalysts, organozinc catalysts, etc. From the viewpoint of the diversity of usable catalyst types, reactivity, and cost, organotin catalysts, organotitanium catalysts, or organozinc catalysts are preferred, and organozinc catalysts are most preferred. That is, the metal of component (B) is preferably selected from one or more of zinc, titanium, and tin, and more preferably zinc. In addition, from the viewpoint of suppressing ligand interference and reducing catalytic activity, it is preferable to use one component (B) alone without mixing.

[0026] Specific examples of organotin catalysts include divalent organotin compounds such as tin octoate and tin naphthenate; tetravalent organotin compounds such as dibutyltin dioctanoate, dibutyltin dilaurate, dibutyltin diacetate, dibutyltin dimaleate, dibutyltin distearate, dioctyltin dilaurate, dioctyltin dineodecanate, dibutyltin dibutyloxide, and dibutyltin bis(triethoxysilicate); and chelated tin compounds such as dibutyltin bis(acetylacetone) and other tin-based chelating compounds, but these are not limited to these examples.

[0027] Specific examples of organotitanium catalysts include tetraisopropyl titanate, tetra-n-butyl titanate, tetrabutyl titanate dimer, tetraoctyl titanate, titanium acetylacetone, titanium octylene glycolate, titanium tetraacetylacetone, titanium ethyl acetoacetate, titanium polyhydroxystearate, titanium lactate, titanium triethanolamine, and diisopropyl bis(ethyl acetoacetate) titanate, but are not limited to these.

[0028] (B) The component can be an organozirconium catalyst. Specific examples of organozirconium catalysts include zirconium tetra-n-propoxide, zirconium tetra-n-butoxide, zirconium tetraacetylacetonate, zirconium monobutoxyacetylacetonate bis(ethyl acetoacetate)zirconium, zirconium dibutoxyacetylacetonate bis(ethyl acetoacetate)zirconium, zirconium tributoxystearate, etc., but are not limited to these.

[0029] Specific examples of organozinc catalysts include zinc (1-butylimidazolium)2(acetate)2, zinc (1-methylimidazolium)2(acetate)2, zinc (imidazolium)2(acetate)2, zinc (1,2-dimethylimidazolium)2(acetate)2, zinc (tetramethylguanidine)2(acetate)2, zinc (DBN)2(acetate)2, zinc (DBU)2(acetate)2, zinc (1-butylimidazolium)2(acetate)2, zinc (1-methylimidazolium)2(formate)2, zinc (imidazolium)2(formate)2, and zinc (1,2-dimethylimidazolium)2(formate). Zinc(tetramethylguanidine)2(formate)2, zinc(DBN)2(formate)2, zinc(DBU)2(formate)2, zinc(1-butylimidazolium)2(neodecanate)2, zinc(1-methylimidazolium)2(neodecanate)2, zinc(imidazolium)2(neodecanate)2, zinc(1,2-dimethylimidazolium)2(neodecanate)2, zinc(tetramethylguanidine)2(neodecanate)2, zinc(DBN)2(neodecanate)2, zinc(DBU)2(neodecanate)2, etc., but not limited to these. Here, DBN represents 1,5-diazabicyclo[4.3.0]non-5-ene, and DBU represents 1,8-diazabicyclo[5.4.0]undec-7-ene.

[0030] Examples of organozinc catalysts include complex compounds with zinc (divalent) as the central metal. When component (B) above contains a ligand, examples of ligands include amine compounds, carboxylate compounds, β-keto ester compounds, and β-diketo compounds, among which amine compounds and carboxylate compounds are preferred.

[0031] Examples of the aforementioned carboxylate compounds include acetic acid, formic acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, octanoic acid, azelaic acid, sebacic acid, and neodecanoic acid. Examples of the aforementioned β-keto ester compounds include methyl acetoacetate, ethyl acetoacetate, n-propyl acetoacetate, isopropyl acetoacetate, n-butyl acetoacetate, sec-butyl acetoacetate, and tert-butyl acetoacetate. Examples of the aforementioned β-diketone compounds include acetylacetone, hexane-2,4-dione, heptane-2,4-dione, heptane-3,5-dione, octane-2,4-dione, nonane-2,4-dione, and 5-methyl-hexane-2,4-dione. Examples of the aforementioned amine compounds include alkylamine compounds such as n-propylamine, isopropylamine, n-butylamine, n-hexylamine, n-octylamine, 2-ethylhexylamine, n-decylamine, and n-dodecaneamine. They can be used alone or in combination of two or more. As component (B), zinc alkylamine complexes are particularly preferred. Zinc alkylamine complexes are organozinc catalysts in which alkylamine compounds are coordinated to zinc.

[0032] (B) The component may be added in the form of a composition obtained by mixing with curing accelerators, plasticizers, solvents, etc., as described below.

[0033] There are no particular restrictions on commercially available organic zinc catalysts. Examples include K-KAT 670 and K-KAT XK-648 manufactured by KING INDUSTRIES, and Borchi (registered trademark) Kat 0244, Borchi (registered trademark) Kat 15, and Borchi (registered trademark) Kat 22 manufactured by OMG Borchers GmbH, but these are not the only options available.

[0034] Component (B) of the present invention is particularly preferably an organozinc catalyst. By combining the organozinc catalyst with components other than component (B), such as components (A) and (C) of the present invention, the cured product can achieve significant effects such as higher elongation, higher strength, and better heat resistance.

[0035] In the moisture-curing composition of the present invention, the amount of component (B) (the total amount when it includes two or more components) relative to 100 parts by weight of component (A) is, for example, 0.01 to 25 parts by weight, more preferably 0.01 to 20 parts by weight, even more preferably 0.01 to 10 parts by weight, and even more preferably 1 to 5 parts by weight. Within the above range, the cured product of the moisture-curing composition exhibits higher elongation, higher strength, and superior heat resistance.

[0036] <(C) Ingredients>

[0037] The component (C) that can be used in this invention is an aromatic secondary amine compound. Component (C) has the effect of acting as an antioxidant. It should be noted that component (C) does not contain component (B) as described above. Specifically, component (C) is preferably a compound having any of the structures of general formulas 1 to 3.

[0038] [Chemical Formula 1]

[0039] In general formulas 1 to 3, Ar independently represents an aromatic hydrocarbon group, and R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkynyl group.

[0040] In general formulas 1 to 3 above, the aromatic hydrocarbon group represented by Ar can be independently a monocyclic aromatic hydrocarbon group or a polycyclic aromatic hydrocarbon group. Specific examples of Ar include groups derived from benzene rings, naphthyl rings, etc. Preferably, Ar can be independently a benzene ring group or a naphthyl ring group. It should be noted that in general formulas 1 to 3 above, the aromatic hydrocarbon group represented by Ar may have substituents on the aromatic ring in addition to N or R of the above formulas, but it is preferable that it does not have substituents other than these. In addition, the aromatic hydrocarbon group represented by Ar may have a linking group between the aromatic ring and N or R of the above formulas, but it is preferable that it does not have a linking group.

[0041] In general formulas 1 to 3 above, R is each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkynyl group. Examples of alkyl groups include those with 1 to 10 carbon atoms. Examples of cycloalkyl groups include those with 3 to 10 carbon atoms. Examples of alkenyl groups include those with 1 to 10 carbon atoms. Examples of alkynyl groups include those with 1 to 10 carbon atoms.

[0042] Examples of substituents for the aforementioned alkyl, cycloalkyl, alkenyl, and alkynyl groups include halogen atoms, hydroxyl groups, amino groups, alkoxy groups, alkylamino groups, alkylsulfonyl groups, (meth)acryloyl groups, (meth)acryloyloxy groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted arylalkyl groups containing aromatic rings, but are not limited to these.

[0043] By adding component (C), the cured product exhibits high elongation, high strength, and excellent heat resistance. Specific examples of component (C) are not particularly limited, and include phenylenediamine-based antioxidants, diphenylamine-based antioxidants, etc. Among these, phenylenediamine-based antioxidants represented by general formula 1 or 3, and diphenylamine-based antioxidants represented by general formula 2 are preferred. Considering the hardness, tensile strength, elongation, and tensile shear bond strength of the cured product during heat resistance testing, phenylenediamine-based antioxidants represented by general formula 1 or 3 are most preferred. Component (C) can be used alone or in combination of two or more.

[0044] Specific examples of phenylenediamine-based antioxidants represented by the above general formula 1 include N,N'-di-2-naphthyl-p-phenylenediamine and N,N'-diphenyl-p-phenylenediamine, but they are not limited to these. From the perspective of superior heat resistance, N,N'-di-2-naphthyl-p-phenylenediamine is particularly preferred.

[0045] Specific examples of the diphenylamine-based antioxidants represented by the above general formula 2 include 4,4'-bis(α,α-dimethylbenzyl)diphenylamine, 4,4'-stilbene diphenylamine, 4,4'-dioctyl diphenylamine, octylated diphenylamine, 4-(α-phenylethyl)diphenylamine, 4,4'-bis(α-phenylethyl)diphenylamine, di-tert-butyl diphenylamine, N-phenyl-1-naphthylamine, etc., but are not limited to these. From the perspective of superior heat resistance, 4,4'-bis(α,α-dimethylbenzyl)diphenylamine, 4,4'-stilbene diphenylamine, 4,4'-dioctyl diphenylamine, or octylated diphenylamine are preferred, and 4,4'-bis(α,α-dimethylbenzyl)diphenylamine is particularly preferred.

[0046] Specific examples of the phenylenediamine-based antioxidants represented by the above general formula 3 include N-isopropyl-N'-phenyl-p-phenylenediamine, N-phenyl-N'-(3-methacryloyloxy-2-hydroxypropyl)-p-phenylenediamine, 2-[(mercaptoacetyl)oxy]ethyl-3-[[4-(phenylamino)phenyl]amino]butyrate, N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine, N-cyclohexyl-N'-phenyl-p-phenylenediamine, phenyl-octyl-p-phenylenediamine, bis(phenyl-isopropylidene)-4,4-diphenylamine, N-(3-methacryloyloxy-2-hydroxypropyl)-N'-phenyl-p-phenylenediamine, N-isopropyl-N'-p-phenylenediamine, etc., but are not limited to these. From the perspective of excellent heat resistance, N-isopropyl-N'-phenyl-p-phenylenediamine or N-phenyl-N'-(3-methacryloyloxy-2-hydroxypropyl)-p-phenylenediamine is preferred.

[0047] It should be noted that, as component (C), aromatic secondary amine compounds other than those represented by general formulas 1 to 3 may also be used. Examples of such aromatic secondary amine compounds include N,N'-bis(1-methylheptyl)-p-phenylenediamine, N,N-bis(1,4-dimethylpentyl)-p-phenylenediamine, 2,4,6-tris(N-1,4-dimethylpentyl-p-phenylenediamine)1,3,5-triazine, diallyl-p-phenylenediamine mixtures, p-(p-toluenesulfonamide)diphenylamine, 4-(anilinophenyl)methacrylamide, etc.

[0048] Commercially available products as component (C) include, for example, the NOCRAC series manufactured by Ouchi Shinsei Chemical Co., Ltd., such as NOCRAC PA (N-phenyl-1-naphthylamine), NOCRAC ODA, NOCRAC ODA-N, NOCRAC AD-F (octyl diphenylamine), NOCRAC CD (4,4'-bis(α,α-dimethylbenzyl)diphenylamine), NOCRAC TD (p-(p-toluenesulfonamide)diphenylamine), NOCRAC White (N,N'-di-2-naphthyl-p-phenylenediamine), NOCRAC 810-NA (N-isopropyl-N'-p-phenylenediamine), NOCRAC 6C (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine), NOCRAC... G-1 (N-phenyl-N'-(3-methacryloyloxy-2-hydroxypropyl)-N'-phenyl-p-phenylenediamine), etc., can be exemplified by NONFLEX OD-3, NONFLEX DCD, STEARER LAS, etc. manufactured by Seiko Chemical Co., Ltd., but is not limited to these.

[0049] In the moisture-curing composition of the present invention, the amount (content, the total amount when containing two or more components) of component (C) is preferably 0.01 to 20 parts by mass relative to 100 parts by mass of component (A) (the total amount when containing two or more components). More preferably, it is 0.5 to 5 parts by mass, and even more preferably, it is 0.5 to 2 parts by mass. If more than 0.01 parts by mass of component (C) are added relative to 100 parts by mass of component (A), the heat resistance of the cured product is further improved. If the amount added is less than 20 parts by mass, the elongation and strength of the cured product are higher.

[0050] <Any ingredient>

[0051] For the moisture-curing compositions of the present invention, additives such as curing accelerators, thioether-based antioxidants, fillers, silane compounds having alkoxysilyl groups (excluding component (A)) may be used without prejudice to the purpose of the present invention.

[0052] Examples of curing accelerators include amine compounds. Specifically, primary amines, secondary amines, and tertiary amines are examples. However, the curing accelerator does not include component (B) above. Furthermore, the curing accelerator does not include component (C) above. Examples of primary amines include N-propylamine, N-isopropylamine, N-butylamine, N-benzylamine, N-hexylamine, N-cyclohexylamine, N-n-octylamine, N-(2-ethylhexyl)amine, N-(2-phenylethyl)amine, N-(3-methoxypropyl)amine, N-decylamine, N-dodecylamine, and ethylenediamine, etc. Examples of secondary amines include N,N-dipropylamine, N,N-diisopropylamine, N,N-dibutylamine, N,N-dihexylamine, N,N-dicyclohexylamine, N,N-bis(2-methoxyethyl)amine, N,N-dioctylamine, N,N-bis(2-ethylhexyl)amine, N,N-diisononylamine, N,N-bis(tetrazyl)amine, morpholine, 2,2,6,6-tetramethylpiperidine, N,N'-dimethylethylenediamine, N,N'-diethylethylenediamine, and N,N'-diisopropylethylenediamine. Examples of tertiary amines include 3-diethylaminopropylamine, imidazole, 1-methylimidazolium, 1-butylimidazolium, 1,2-dimethylimidazolium, tetramethylguanidine, DBU, and DBN.

[0053] The moisture-curing composition of the present invention may further include a thioether-based antioxidant. By combining the thioether-based antioxidant with the above-described component (C) of the present invention, the cured product exhibits higher elongation, higher strength, and superior heat resistance. Examples of thioether-based antioxidants include pentaerythritol tetra[3-(dodecylthio)propionate] ester, pentaerythritol tetra(3-lauryl thiopropionate), dilauryl 3,3'-thiodipropionate, dimyristyl 3,3'-thiodipropionate, and distearate 3,3'-thiodipropionate. The thioether-based antioxidant may be only one type or two or more types. Commercially available thioether-based antioxidants include, for example, ADK STAB AO-503, AO-26, and AO-412S (manufactured by ADEKA CORPORATION).

[0054] When the moisture-curing composition contains a thioether-based antioxidant, the amount of the thioether-based antioxidant added (the total amount when containing two or more types) is not particularly limited, but is preferably 0.1 to 10 parts by weight, more preferably 0.5 to 5 parts by weight, relative to 100 parts by weight of component (A) (the total amount when containing two or more types). Furthermore, the content of the aforementioned thioether-based antioxidant (the total amount when containing two or more types) is preferably 0.1 to 10 parts by weight, particularly preferably 0.5 to 5 parts by weight, relative to 1 part by weight of component (C) (the total amount when containing two or more types). Within the above range, the cured product exhibits superior heat resistance.

[0055] Specific examples of fillers include talc powder, silica powder, clay powder, calcium carbonate powder, magnesium carbonate powder, calcium silicate powder, glass powder, alumina powder, zinc oxide powder, magnesium oxide powder, aluminum nitride powder, boron nitride powder, and aluminum hydroxide powder. Additionally, fillers may be surface-treated with fatty acid soaps, etc. Furthermore, they can be used alone or in combination. Among these, talc powder, silica powder, clay powder, calcium carbonate powder, magnesium carbonate powder, calcium silicate powder, and glass powder are preferred to impart high modulus to the cured product, with calcium carbonate powder being particularly preferred. Furthermore, calcium carbonate powder that has undergone surface treatment with fatty acid soaps, etc., is preferred. From the perspective of achieving higher elongation, higher strength, and better heat resistance in the cured product, it is further preferred to use a combination of surface-treated and untreated calcium carbonate powder. Furthermore, to impart thermal conductivity to the moisture-curing composition, fillers with thermal conductivity such as alumina powder, zinc oxide powder, magnesium oxide powder, aluminum nitride powder, and boron nitride powder are preferred; to impart flame retardancy to the moisture-curing composition, aluminum hydroxide powder is preferred. By imparting thermal conductivity to the moisture-curing composition, it can be used as a heat dissipation agent exhibiting thermal conductivity.

[0056] From the viewpoint of achieving higher elongation, higher strength, and superior heat resistance in the cured product, the average particle size of the filler is preferably 0.001 to 90 μm, more preferably 0.005 to 50 μm, and most preferably 0.01 to 20 μm. Furthermore, it is preferable to mix a filler with an average particle size of 0.5 μm or more and 90 μm or less with a filler with an average particle size of 0.001 μm or more and less than 0.5 μm. The mixture contains, more preferably, 100 to 300 parts by mass of the filler with an average particle size of 0.001 μm or more and less than 0.5 μm, more preferably 150 to 250 parts by mass, and even more preferably 200 to 240 parts by mass, relative to 100 parts by mass of the filler with an average particle size of 0.5 μm or more and 90 μm or less. It should be noted that in this invention, the average particle size is the particle size at which the cumulative 50% of the particle size distribution is measured by laser diffraction and scattering. The particle size at which the cumulative 50% of the measured particle size distribution is taken is also called the 50% average particle size or D50.

[0057] In a preferred embodiment, the moisture-curing composition comprises untreated calcium carbonate powder with an average particle size of 0.5 μm or more and 90 μm or less, and calcium carbonate powder with an average particle size of 0.001 μm or more and less than 0.5 μm as fillers. In this case, relative to 100 parts by weight of the untreated calcium carbonate powder with an average particle size of 0.5 μm or more and 90 μm or less, it is preferable to include 100 to 300 parts by weight of the calcium carbonate powder with an average particle size of 0.001 μm or more and less than 0.5 μm, more preferably 150 to 250 parts by weight, and even more preferably 200 to 240 parts by weight.

[0058] The amount of filler (the total amount when containing two or more types) relative to 100 parts by weight of component (A) is preferably in the range of 2 to 400 parts by weight, more preferably 10 to 300 parts by weight, even more preferably 30 to 200 parts by weight, even more preferably 100 to 200 parts by weight, and particularly preferably 140 to 180 parts by weight. Within the above range, the cured product exhibits higher elongation, higher strength, and superior heat resistance.

[0059] When using thermally conductive fillers such as alumina powder, zinc oxide powder, magnesium oxide powder, aluminum nitride powder, and boron nitride powder as fillers, the content of the thermally conductive filler is not particularly limited. For example, it is preferably 55% to 95% by mass, more preferably 60% to 90% by mass, relative to the total amount of the moisture-curing composition.

[0060] The aforementioned thermally conductive filler is preferably combined with two or more thermally conductive fillers having different average particle sizes. This results in a moisture-curing composition with superior thermal conductivity in the cured product. For example, it is preferable to combine a thermally conductive filler with an average particle size of 0.001 μm or more and less than 5 μm, and a thermally conductive filler with an average particle size of 5 μm or more and less than 90 μm. In this case, the content of the thermally conductive filler with an average particle size of 5 μm or more and less than 90 μm is, for example, 10 to 700 parts by weight, preferably 100 to 500 parts by weight, relative to 100 parts by weight of the thermally conductive filler with an average particle size of 0.001 μm or more and less than 5 μm.

[0061] In other preferred embodiments, thermally conductive fillers with an average particle size of 0.001 μm or more and less than 5 μm, thermally conductive fillers with an average particle size of 5 μm or more and less than 20 μm, and thermally conductive fillers with an average particle size of 20 μm or more and less than 90 μm can be used together. In this case, relative to 100 parts by weight of the thermally conductive filler with an average particle size of 0.001 μm or more and less than 5 μm, the content of the thermally conductive filler with an average particle size of 5 μm or more and less than 20 μm is, for example, 5 to 600 parts by weight, preferably 110 to 200 parts by weight. Furthermore, relative to 100 parts by weight of the thermally conductive filler with an average particle size of 0.001 μm or more and less than 5 μm, the content of the thermally conductive filler with an average particle size of 20 μm or more and less than 90 μm is, for example, 5 to 600 parts by weight, preferably 200 to 400 parts by weight.

[0062] The above-mentioned silane compounds having alkoxysilyl groups do not include component (A), and in particular refer to silane compounds with a molecular weight of less than 1000. Specific examples of silane compounds containing alkoxysilane groups include silicate esters such as methyl silicate, ethyl silicate, propyl silicate, and butyl silicate; alkyl-containing silane coupling agents such as dimethyldimethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, and hexyltrimethoxysilane; vinyl-containing silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; phenyl-containing silane coupling agents such as phenyltrimethoxysilane, diphenyldimethoxysilane, and phenyltriethoxysilane; and N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyltrimethoxysilane, and N-2-(aminoethyl)-3-aminopropylmethyltriethoxysilane. Silane coupling agents containing amino groups, such as silane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and N-phenyl-3-aminopropyltrimethoxysilane; silane coupling agents containing glycidyl groups, such as 3-epoxypropoxypropylmethyldimethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, and 3-epoxypropoxysilyltriethoxysilane; and silane coupling agents containing (meth)acryloyl groups, such as 3-(meth)acryloyloxypropylmethyldimethoxysilane, 3-(meth)acryloyloxypropylmethyldiethoxysilane, and 3-(meth)acryloyloxypropyltriethoxysilane. Among these, silane coupling agents containing amino groups or glycidyl groups are preferred because the cured products exhibit higher elongation, higher strength, and superior heat resistance. Furthermore, the amount of the aforementioned silane compound containing alkoxysilyl groups (the total amount when including two or more) relative to 100 parts by mass of component (A) is preferably in the range of 0.1 to 25 parts by mass, more preferably 0.3 to 20 parts by mass, and particularly preferably 0.5 to 18 parts by mass. Within the above range, the cured product exhibits higher elongation, higher strength, and superior heat resistance, and is therefore preferred.

[0063] Specific examples of the aforementioned plasticizers are broadly classified into phthalate-based plasticizers and non-phthalate-based plasticizers. From the perspective of low carcinogenicity and maintaining the effects of the present invention, non-phthalate-based plasticizers are preferred. There are no particular limitations on the aforementioned non-phthalate-based plasticizers; examples include (meth)acrylic acid polymer-based plasticizers obtained by polymerizing (meth)acrylic acid monomers; polyether polyol-based plasticizers such as polyethylene glycol, polypropylene glycol, and polytetramethylene glycol; polyester-based plasticizers obtained from dibasic acids such as sebacic acid and adipic acid with diols such as ethylene glycol, diethylene glycol, triethylene glycol, and propylene glycol; processing oil-based plasticizers; and alkyl sulfonates, tributyl acetylated citrate, etc. The viscosity of the plasticizer at 25°C is not particularly limited, and is, for example, 0.1 to 5 Pa·s. Furthermore, the amount of plasticizer added (the total amount when including two or more types) is preferably in the range of 5 to 300 parts by weight relative to 100 parts by weight of component (A) of the present invention (the total amount when including two or more types). More preferably, it is in the range of 10 to 150 parts by weight, and particularly preferably, it is in the range of 12 to 75 parts by weight. Within the above range, the cured product has higher elongation, higher strength, and better heat resistance.

[0064] Specific examples of the solvents mentioned above include ketone solvents, alcohol solvents, glycol solvents, hydrocarbon solvents, and ester solvents.

[0065] There are no particular limitations on the dispersant used, but from the viewpoint of easily improving the dispersibility of components (A) to (C) above, hydroxyl-containing carboxylic acid esters are preferred. The dispersant can be either synthetic or commercially available. Specific examples of commercially available products include the DISPER BYK (registered trademark) series manufactured by BYK Corporation. There are no particular limitations on the content of the dispersant, for example, 0.01 to 20 parts by weight relative to 100 parts by weight of component (A).

[0066] <Curing methods and cured products>

[0067] The moisture-curing composition of the present invention can be formulated as a one-component or two-component composition. Here, two-component refers to a form in which two components are mixed and cured during use. Curing can be achieved by adjusting the humidity and temperature of the external air. Alternatively, curing can be achieved by heating using a hot air drying oven or the like. Specific curing conditions, for example, preferably include a temperature in the range of 5°C to 50°C, a humidity in the range of 40%RH to 70%RH, and a curing time in the range of 5 minutes to 10 days. Furthermore, a cured product obtained by curing the moisture-curing composition of the present invention is also an aspect of the present invention. That is, the present invention also provides a cured product obtained by curing the above-described moisture-curing composition.

[0068] <Applications>

[0069] The moisture-curing composition of the present invention is preferred for various applications such as adhesives, sealants, potting compounds, coating agents, thermally conductive resins, flame-retardant resins, and conductive pastes because its cured product has high elongation, high strength, and excellent heat resistance. In particular, it is preferred for applications such as automotive parts, electrical and electronic components, and building materials.

[0070] Examples of automotive components mentioned above include oil pans, transmissions, oil pressure switches, air flow meters, cam position sensors, water temperature sensors, crankshaft position sensors, intake air temperature sensors, vehicle speed sensors, automotive electronic boards, nickel batteries, Li batteries, and fuel cells. Adhesives, sealants, and potting compounds using the moisture-curing composition of the present invention can be suitable for use in these components.

[0071] Furthermore, when the moisture-curing composition of the present invention is given thermal conductivity, it can be used for various applications such as heat dissipation of electronic substrates, heat dissipation of electronic devices such as mobile phones and personal computers, heat dissipation of lighting such as LEDs, heat dissipation of optical pickup modules, heat dissipation of camera modules, heat dissipation of sensor devices, heat dissipation of power semiconductors, heat dissipation of inverters, heat dissipation of converters, and heat dissipation of ECU components.

[0072] The moisture-curing composition of the present invention can be used for bonding various substrates. In particular, because of its excellent adhesion to aluminum, it is suitable as an adhesive or sealant for applications using aluminum. Examples of applications using aluminum include backsheets containing aluminum layers, heat sinks, and battery casings used in solar cells.

[0073] <How to use>

[0074] As for sealing methods using the moisture-curing composition of the present invention, there are no particular limitations, and FIPG (Film-in-Situ Gasket) and the like are representative examples. FIPG refers to a method in which the moisture-curing composition of the present invention is applied to the flange of a sealed component using an automatic coating device or the like, and then cured while in contact with another flange to achieve an adhesive seal. More specifically, a sealing method is provided for sealing at least a portion between at least two flanges of a sealed component having at least two flanges, characterized by comprising: a step of applying the moisture-curing composition to the surface of at least one of the flanges; a step of bonding one flange coated with the moisture-curing composition to another flange via the moisture-curing composition; and a step of curing the moisture-curing composition to seal at least a portion between the at least two flanges.

[0075] Example

[0076] The following examples illustrate the invention in more detail, but the invention is not limited to these examples. Hereinafter, the moisture-curing composition will also be referred to simply as the composition.

[0077] [Examples 1-8 and Comparative Examples 1-4]

[0078] <Preparation of Moisture-Curing Compositions>

[0079] To prepare a moisture-curing composition, the following components are prepared.

[0080] (A) Composition: Organic polymers containing two or more alkoxysilyl groups within the molecule.

[0081] • A linear polyoxyethylene with trimethoxysilyl groups at both ends, having a viscosity of 50 Pa·s at 25°C (SKANESA CORPORATION SILYL (registered trademark) SAX 575).

[0082] (B) Components: Organometallic catalyst

[0083] • Zinc alkylamine complex (K-KAT 670 manufactured by King Industries)

[0084] • Diisopropyl bis(ethyl acetoacetate) titanate (manufactured by Matsumoto Fine Chemical Co., Ltd., TC-750)

[0085] • Dioctyltin dilaurate (NEOSTANN U-810 manufactured by Nitto Kasei Corporation)

[0086] (C) Components: Aromatic secondary amine compounds

[0087] ·N,N'-Di-2-naphthyl-p-phenylenediamine (Nocrac White, manufactured by Ouchi Shinsei Chemical Co., Ltd.)

[0088] ·4,4'-Bis(α,α-dimethylbenzyl)diphenylamine (Nocrac CD manufactured by Ouchi Shinsei Chemical Co., Ltd.)

[0089] (C') Ingredient: Antioxidants other than (C) ingredient

[0090] • Liquid sulfide-based antioxidant (AO-26 manufactured by ADEKA CORPORATION)

[0091] • Pentaerythritol tetra[3-(dodecylthio)propionate] ester (AO-412S manufactured by ADEKA CORPORATION)

[0092] Tetrakis[3-(3',5'-di-t-butyl-4'-hydroxyphenyl)propionate] (ADEKA CORPORATION, AO-60)

[0093] filler

[0094] • Untreated calcium carbonate powder with an average particle size of 1.3 μm (SOFTON 1800 manufactured by Bikita Powder Chemical Industry Co., Ltd.)

[0095] • Calcium carbonate powder with an average particle size of 0.05 μm that has been surface-treated with fatty acid soap (KALFAINE 500 manufactured by Maruo Calcium Co., Ltd.).

[0096] In a stirred tank, components (A), (C) (and / or (C')) and the filler were weighed and stirred at 25°C for 60 minutes while undergoing vacuum degassing. Then, component (B) was weighed and added, and the mixture was further stirred at 25°C for 30 minutes while undergoing vacuum degassing to obtain a moisture-curing composition. It should be noted that the detailed preparation quantities are based on Table 1, and all values ​​are expressed in parts by mass. In Table 1, the total is the sum of components (A) through (C) and component (C'). Additionally, in Table 1, blank columns indicate that the corresponding component is not included.

[0097] [Table 1]

[0098] <Evaluation>

[0099] The moisture-curing compositions of Examples 1-8 and Comparative Examples 1-4 were subjected to hardness, tensile strength, elongation (elongation at break), and tensile shear bond strength tests, and then each test was performed after a heat resistance test. The results are summarized in Table 2.

[0100] [Hardness Measurement]

[0101] A 2mm thick frame was made as a spacer on a demolded steel plate, and a moisture-curing composition was applied to it at a uniform thickness. The applied moisture-curing composition was placed at 23°C and 50%RH for 7 days to produce a cured product. Three cured products were stacked to make a test piece. The hardness was tested 5 times using an A-type hardness tester (A hardness) with a pressure of 10N, and the average value was taken as the "hardness (unitless)". Details are based on JIS K 6249:2003. The results are shown in Table 2. In the case that the moisture-curing composition does not contain thermally conductive fillers, the initial hardness of the cured product is preferably softer than A50 (hardness less than 50) if flexibility is taken into consideration.

[0102] [Tensile Strength Test]

[0103] A 2mm thick frame is fabricated as a spacer on a demolded steel plate, and a moisture-curing composition is applied to it with uniform thickness. The applied moisture-curing composition is placed at 23°C and 50%RH for 7 days to produce a cured product. The cured product is punched using a No. 5 dumbbell to produce a test piece. The two ends of the test piece are fixed to a chuck. The test piece is stretched at a tensile speed of 500 mm / min, and the maximum load is measured. The results are shown in Table 2. The strength at this maximum load is defined as "tensile strength (MPa)". For details, refer to JIS K 6251 (2010). In addition, the tensile strength (initial) of the cured product is preferably 1.6 MPa or more, and more preferably 1.7 MPa or more.

[0104] [Elongation (Elongation at Break) Measurement]

[0105] A 2mm thick frame was fabricated as a spacer on a demolded steel plate, and a moisture-curing composition was coated with it to a uniform thickness. The coated moisture-curing composition was placed at 23°C and 50%RH for 7 days to produce a cured product. The cured product was punched with a No. 5 dumbbell to produce a test piece, and 25mm intervals were marked on the test piece. The two ends of the test piece were fixed to a chuck using the same method as for the tensile strength test, and the test piece was stretched at a tensile speed of 500mm / min until the test piece broke. During the test, the test piece elongated, and the intervals of the marks widened. Therefore, the intervals of the marks were measured using vernier calipers until the test piece broke. The elongation percentage of the mark intervals was taken as the "elongation (%)" based on the initial mark intervals. The results were evaluated based on the following criteria and are shown in Table 2. In addition, when the moisture-curing composition does not contain a thermally conductive filler, from the viewpoint of high elongation, the elongation (initial) of the cured product is preferably 250% or more, more preferably 350% or more, and even more preferably 400% or more.

[0106] [Tensile Shear Bond Strength Test]

[0107] Prepare two aluminum plates (A1050P) with a width of 25mm × length of 100mm × thickness of 1mm. Apply a moisture-curing composition to one aluminum plate. Then, attach and fix the other aluminum plate so that the overlap is 25mm wide × 10mm long × 1mm thick. Then, place it in an environment of 23°C and 50%RH for 7 days to prepare a test piece. Fix the above test piece in the chuck of a universal tensile testing machine and stretch it at a tensile speed of 50mm / min. The "tensile shear bond strength (MPa)" is determined by the maximum strength and the bond area. Details are based on JIS K 6850:1999. The results are shown in Table 2. It should be noted that in this invention, the tensile shear bond strength (initial) of the cured product is preferably 1.3MPa or higher.

[0108] [Heat Resistance Test]

[0109] Following the steps described above, test pieces were prepared for hardness testing, tensile strength testing, elongation testing, and tensile shear bond strength testing. The hardness, tensile strength, elongation, and tensile shear bond strength at 0 hours (initial) were then measured. Another test piece was prepared and placed in a hot air drying oven set to 120°C. After 500 hours and 1000 hours, it was removed and allowed to return to room temperature. The hardness, tensile strength, elongation, and tensile shear bond strength were then measured according to the steps described above. The results are shown in Table 2. In Table 2, initial, 500 hours, and 1000 hours represent the measured values ​​at the initial, 500 hours, and 1000 hours, respectively. Furthermore, the "rate of change (%)" was calculated using the formula: rate of change = [(measured value after 1000 hours - initial measured value) / initial measured value] × 100, and is shown in Table 2. The rate of change after 1000 hours is preferably -60% to 60%, more preferably -30% to 30%.

[0110] It should be noted that in Table 2, "-" indicates that the specimen became unmeasurable when exposed to the atmosphere of the heat resistance test. For hardness, tensile strength, and elongation, the cured product of a certain shape became brittle and could not be measured. For tensile shear bond strength, it became unmeasurable because the cured product could not be held in place by clamping it between the aluminum plate used as the bonded material.

[0111] [Table 2]

[0112] Comparing Examples 1-8 with Comparative Examples 1-4, the change rates of Examples 1-8 converged to -60% to 60% in all test items, but thermal degradation occurred in Comparative Examples 1-4. In Comparative Examples 1 and 2, the change rates were unmeasurable after 500 hours in all test items, and in Comparative Examples 3 and 4, the change rates were unmeasurable after 1000 hours in all test items. For Examples 1-8, it is evident that good heat resistance is achieved by using component (C), while as described in Comparative Examples 1-4, sufficient heat resistance was not observed without component (C). As described in Comparative Examples 3 and 4, heat resistance was not improved when only component (C') was used without component (C). In particular, N,N'-di-2-naphthyl-p-phenylenediamine was added as component (C) in Example 1, and the change rates were between -30% and 30% in all test items in Table 2, making it particularly preferred.

[0113] [Example 9]

[0114] <Preparation of Moisture-Curing Compositions>

[0115] To prepare a moisture-curing composition, the following components are prepared.

[0116] (A) Composition: Organic polymers containing two or more alkoxysilyl groups within the molecule.

[0117] • A linear polyoxyethylene with dimethoxysilyl groups at both ends, having a viscosity of 50 Pa·s at 25°C (SKANESA CORPORATION SILYL (registered trademark) SAX750).

[0118] (B) Components: Organometallic catalyst

[0119] • Zinc alkylamine complex (K-KAT 670 manufactured by KINGINDUSTRIES)

[0120] (C) Components: Aromatic secondary amine compounds

[0121] ·4,4'-Bis(α,α-dimethylbenzyl)diphenylamine (NOCRAC CD manufactured by Ouchi Shinsei Chemical Co., Ltd.)

[0122] filler

[0123] • Alumina powder with an average particle size of 0.5 μm (referred to as filler 1 in Table 3 below)

[0124] • Alumina powder with an average particle size of 5.4 μm (referred to as filler 2 in Table 3 below)

[0125] • Alumina powder with an average particle size of 40 μm (referred to as filler 3 in Table 3 below)

[0126] plasticizer

[0127] • An acrylic polymer with a viscosity of 3.5 Pa·s and a weight-average molecular weight of 2500 at 25°C (referred to as plasticizer 1 in Table 3 below).

[0128] Silane coupling agent

[0129] • Methyltrimethoxysilane (reagent)

[0130] dispersant

[0131] • Hydroxyl-containing carboxylic esters (referred to as dispersant 1 in Table 3 below).

[0132] In a stirred tank, weigh components (A), (C), filler, plasticizer, silane coupling agent, and dispersant, and stir with a stirrer at 25°C for 60 minutes while performing vacuum degassing. Then, weigh and add component (B), and further stir at 25°C for 30 minutes while performing vacuum degassing to obtain a moisture-curing composition. It should be noted that the detailed preparation quantities are based on Table 3, and all values ​​are expressed in parts by mass. In Table 3, the total represents the sum of all components.

[0133] [Table 3]

[0134] <Evaluation>

[0135] For the moisture-curing composition of Example 9, hardness, tensile strength, elongation (elongation at break), and tensile shear bond strength were measured using the same methods as those used in Examples 1-8 and Comparative Examples 1-4. Additionally, thermal conductivity was measured using the methods described below. The results obtained as initial hardness, tensile strength, elongation, tensile shear bond strength, and thermal conductivity are shown in Tables 4 and 5 below.

[0136] [Thermal conductivity measurement]

[0137] Thermal conductivity measurements are performed according to the following steps: Apparatus: TRIDENT thermal conductivity measuring apparatus manufactured by C-THERM Test method: ASTM D7984-21 Modified Transient Plane Source (MTPS) Specifically, first, a cured material with a diameter of 18 mm or more and a thickness of 2 mm (n=3) is prepared. Next, a contact liquid is dropped onto the sensor (resistance temperature detector unit), the cured material is placed on top, and a 500g weight is placed on it. Water is used as the contact liquid. Then, the thermal conductivity at 25°C is measured.

[0138] It should be noted that in the moisture-curing composition containing a thermally conductive filler, the initial hardness of the cured product is preferably 100 or less. The initial elongation of the cured product is preferably 80% or more. The preferred values ​​for the initial tensile strength and tensile shear bond strength of the cured product are the same as those described above. In addition, the initial thermal conductivity of the cured product is preferably 2.5 W / m·K or more.

[0139] Furthermore, for each test piece used for hardness testing, tensile strength testing, elongation (elongation at break) testing, tensile shear bond strength testing, and thermal conductivity testing, a heat resistance test was conducted at 120°C using the same method as the heat resistance test in Examples 1-8 and Comparative Examples 1-4 above. However, the placement time was set to 240 hours, 500 hours, 750 hours, and 1000 hours, and the results are summarized in Table 4.

[0140] In addition, for each test piece used for hardness testing, tensile strength testing, elongation (elongation at break) testing, tensile shear bond strength testing, and thermal conductivity testing, they were placed in a constant temperature and humidity bath set at 85°C and 85%RH for 240 hours, 500 hours, 750 hours, and 1000 hours, respectively, and then removed and allowed to return to room temperature. The hardness, tensile strength, elongation, tensile shear bond strength, and thermal conductivity tests were then performed according to the above steps. The results are summarized in Table 5.

[0141] [Table 4]

[0142] [Table 5]

[0143] As shown in Tables 4 and 5 above, the moisture-curing composition of Example 9 exhibits excellent properties in terms of hardness, tensile strength, elongation (elongation at break), tensile shear bond strength, and thermal conductivity. Furthermore, in all these tests, the rate of change after 1000 hours of heat resistance testing at 120°C is in the range of -20% to 20%, demonstrating excellent heat resistance. Moreover, in all these tests, the rate of change after 1000 hours of high-temperature and high-humidity resistance testing at 85°C and 85%RH is in the range of -25% to 25%, demonstrating excellent high-temperature and high-humidity resistance.

[0144] Industrial applicability

[0145] The moisture-curing composition of the present invention produces a cured product with high elongation, high strength, and excellent heat resistance, making it suitable for various applications such as adhesives, sealants, potting compounds, coating agents, thermally conductive resins, flame-retardant resins, and conductive pastes. Therefore, the moisture-curing composition of the present invention can be applied to a wide range of fields and is thus industrially useful.

[0146] This application is based on Japanese Patent Application No. 2023-195483, filed on November 16, 2023, the disclosure of which is referenced and incorporated herein by reference in its entirety.

Claims

1. A moisture-curing composition comprising the following components (A) to (C), (A) Composition: An organic polymer containing two or more alkoxysilyl groups within its molecule. (B) Components: Organometallic catalyst, (C) Components: Aromatic secondary amine compounds.

2. The moisture-curing composition according to claim 1, wherein, The metal in component (B) is selected from one or more of zinc, titanium and tin.

3. The moisture-curing composition according to claim 2, wherein, The metal in component (B) is zinc.

4. The moisture-curing composition according to claim 1, wherein, The (C) component has any one of the following general formulas 1 to 3, [Chemical Formula 1] In general formulas 1 to 3, Ar independently represents an aromatic hydrocarbon group, and R independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, or a substituted or unsubstituted alkynyl group.

5. The moisture-curing composition according to claim 1, wherein, The component (C) contains N,N'-di-2-naphthyl-p-phenylenediamine or 4,4'-bis(α,α-dimethylbenzyl)diphenylamine.

6. The moisture-curing composition according to claim 1, wherein, The main chain of the organic polymer of component (A) is polyoxyethylene or poly(meth)acrylate.

7. The moisture-curing composition according to claim 1, wherein, The organic polymer of component (A) is linear and has alkoxysilyl groups at both ends.

8. The moisture-curing composition according to claim 1, wherein, The content of component (C) is 0.01 to 20 parts by mass relative to 100 parts by mass of component (A).

9. A cured product formed by curing the wet-curing composition of claim 1.

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